Sodium Chloride → HCID 70615499, compound

HRID 1763916Notes

Reaction equation

HRID 1763916 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH2:17][C:18]([OH:25])([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:26])C.COCCOC.[OH-].[K+].[Na+].[Cl-]>C(OCC)C.O>[OH:26][C@H:12]1[CH2:13][CH2:14][C:15](=[CH:16][CH2:17][C:18]([OH:25])([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:27])=[O:3]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 80711,2-DimethoxyethaneHCID 14797Potassium HydroxideHCID 70615461HCID 70615461, compound

Product 1

HCID 70615499HCID 70615499, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 250 mg. 9β,15-dihydroxy-15-methyl-12-prostenoic acid ethyl ester (as mixture of the two 15-epimers), 20 ml. 1,2-dimethoxyethane, 0.3 g. KOH and 5 ml. water is stirred for 12 hours at room temperature, diluted with 40 ml. diethyl ether and saturated with NaCl. The organic phase is separated, washed twice with 15 ml. amounts of H2O and dried over MgSO4. Solvent is removed to obtain, as oily residue, 9α,15-dihydroxy-15-methyl-12-prostenoic acid as mixture of the 15-epimers.

Workup

  1. additionA mixture of 250 mg
  2. additiondiluted with 40 ml
  3. customThe organic phase is separated
  4. washwashed twice with 15 ml
  5. dry with materialamounts of H2O and dried over MgSO4
  6. customSolvent is removed

Sources & evidence

ORD record
ord-a389cc46c8af4e56bfe5b756515c77e3
Source dataset
uspto-grants-1978_09
Patent number
US04113863

Reaction notes

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